US4324901A - Soluble polysilastyrene and method for preparation - Google Patents
Soluble polysilastyrene and method for preparation Download PDFInfo
- Publication number
- US4324901A US4324901A US06/258,663 US25866381A US4324901A US 4324901 A US4324901 A US 4324901A US 25866381 A US25866381 A US 25866381A US 4324901 A US4324901 A US 4324901A
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- US
- United States
- Prior art keywords
- sodium
- reaction
- polysilastyrene
- solvent
- carried out
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- Expired - Fee Related
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/60—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which all the silicon atoms are connected by linkages other than oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
Definitions
- This invention relates to polysilastyrenes and to a method for the preparation of same.
- a solvent use can be made of any non-acidic solvent, or other solvent that does not react with sodium or with the chlorosilanes, in which the monomers are soluble and which has a boiling point above 100° C. It is preferred to make use of toluene as the solvent since it has a boiling point just above the melting point of the sodium and because it is readily available at low cost; however, other organic solvents, such as xylene, mesitylene, n-octane, decalin, and other higher alkanes can be used.
- potassium when present in small amounts, causes polymer degradation and thus can be employed in such small amounts with sodium when it is desired to produce a lower molecular weight polysilastyrene of waxy consistency.
- Utilization of potassium in large amounts, as in the form of a sodium-potassium alloy (78% K) or pure potassium, as in the aforementioned application, will result in extensive cross linking to produce an insoluble and infusible polymer. Thus the amount of potassium should not exceed 1% by weight.
- the monomers are mixed for reaction in substantially equal molecular proportions and the reaction to produce the polymer is carried out at reflux temperature, and preferably at a temperature of about 100° C. for a period of time that may range up to 24 hours. Higher temperatures up to 150° C. can be employed but without any distinct advantage from the standpoint of reaction rate.
- FIG. 1 of the drawings is an illustration of a laboratory setup for the preparation of polysilastyrene polymers in accordance with the practice of this invention.
- FIG. 2 is an example of a molecular weight distribution curve of the polysilastyrene polymers produced by this invention.
- An assembly is made of a 2 liter, 3-necked flask 10 a 500 ml. addition funnel 12, a Davies double jacketed condenser 14, and a motor driven stirrer 16, as illustrated in the FIG. 1 of the drawing.
- the reaction is carried out in an inert atmosphere of dry nitrogen or argon which is circulated through the flask from a gas inlet 18 to a gas outlet 20.
- Reflux temperature is maintained by lowering the heating mantle from the flask when the chlorosilanes are added rapidly enough for exothermic reaction. Addition of the chlorosilane should be completed within a 15 minute period.
- Refluxing is continued with gentle stirring for about 10 hours after which the reaction is quenched by cooling the flask to room temperature and by slow addition of ethanol (95%).
- Addition is then made of an aqueous solution of sodium bicarbonate and/or an aqueous solution of ammonium chloride to discharge the blue color.
- the mixture is agitated until the color of the formed organic layer turns milky white. In the event that the blue color remains, the organic layer can be separated from the aqueous layer and fresh aqueous sodium bicarbonate added thereto with stirring.
- the separated organic layer is stripped of solvent, as by vacuum distillation, and the polymer remaining is washed with water to remove salt residues. At all times the organic layer is protected from light.
- the resulting polymer obtained in a yield of about 90% or more, can be fractionated, as by solvent separation in xylene, to leave a polysilastyrene residue that is soluble in hydrocarbon solvents and especially tetrahydrofuran.
- the polysilastyrene can be fractionated from a tetrahydrofuran-isopropanol system to give high molecular weight fraction numbers averaging as much as 350,000 molecular weight, and oligomers in the form of a viscous oil.
- the yield is typically 60% polymer and about 30% cyclic oligomers having the formula
- At least 90% by weight of the formed polymer is soluble in an organic solvent such as alkylbenzenes, chlorocarbons and tetrahydrofuranes.
- an organic solvent such as alkylbenzenes, chlorocarbons and tetrahydrofuranes.
- polysilastyrene polymers prepared in accordance with the practice of this invention can be formed into solids, films, fibers or the polymer can be molded, cast, or spun from hot melt or from solution in suitable solvents.
- the polysilastyrene polymers of this invention can be used as percursors for making silicon carbide fibers, as described in the aforementioned copending application.
- the polymers can be formed into fibers, sheets and bulk shapes followed by thermolysis under inert conditions at temperatures of about 1200° C. to convert the polymer to silicon carbide in fiber, sheet and bulk shape form as represented by the following equation: ##STR2##
- the polymers of this invention also find beneficial use in gas chromatography separation phases.
- Inert supports coated with the polysilastyrene can be used as a packaging in columns for separation of gas streams composed of mixtures of nonpolar compounds at temperatures for the polysilastyrene such as 300° C.
- Polysilastyrene powders of less than 40 ⁇ are suitable for use in liquid chromatography wherein use is made of a carrier in the form of a solvent in which the polymer is inert, such as alcohol, pentane, methyl cyanide or water.
- the polysilastyrene polymers of this invention can be dissolved in suitable solvents, such as carbon tetrachloride, toluene, or tetrahydrofuran for use as a coating material or as an impregnating material. It is particularly suitable for use as a coating for siliceous materials wherein a strong bonding relation can be established with the silicon oxide groups at the surface of the siliceous material. Ceramics can be strengthened by coating or impregnating with the polymers of this invention and subsequent firing to transform the polymer into silicon carbide.
- Thin films which can be formed of the polysilastyrene polymers of this invention, as by pressure molding or casting from solution are characterized as good insulators ( ⁇ 10 -12 ⁇ -1 cm -1 conductivity) while the conductivity can be increased materially by doping with antimonypentafluoride (SbF 5 ) or arsenic pentafluoride (AsF 5 ).
Abstract
Description
Si.sub.5 Me.sub.10-x Ph.sub.x in which x=0-4
Claims (11)
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/258,663 US4324901A (en) | 1981-04-29 | 1981-04-29 | Soluble polysilastyrene and method for preparation |
PCT/US1982/000357 WO1982003862A1 (en) | 1981-04-29 | 1982-03-19 | Soluble polysilastyrene and method for preparation |
EP82901331A EP0077794A1 (en) | 1981-04-29 | 1982-03-19 | Soluble polysilastyrene and method for preparation |
AU83917/82A AU8391782A (en) | 1981-04-29 | 1982-03-19 | Soluble polysilastyrene and method for preparation |
GB08232287A GB2112009A (en) | 1981-04-29 | 1982-03-19 | Soluble polysilastyrene and method for preparation |
IT48210/82A IT1147840B (en) | 1981-04-29 | 1982-04-09 | PROCEDURE FOR PRODUCING SOLUBLE POLYSYLASTYRENE AND PRODUCT OBTAINED |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/258,663 US4324901A (en) | 1981-04-29 | 1981-04-29 | Soluble polysilastyrene and method for preparation |
Publications (1)
Publication Number | Publication Date |
---|---|
US4324901A true US4324901A (en) | 1982-04-13 |
Family
ID=22981576
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/258,663 Expired - Fee Related US4324901A (en) | 1981-04-29 | 1981-04-29 | Soluble polysilastyrene and method for preparation |
Country Status (5)
Country | Link |
---|---|
US (1) | US4324901A (en) |
EP (1) | EP0077794A1 (en) |
GB (1) | GB2112009A (en) |
IT (1) | IT1147840B (en) |
WO (1) | WO1982003862A1 (en) |
Cited By (55)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3511615A1 (en) * | 1984-04-05 | 1985-10-17 | United States Department Of Energy, Washington, D.C. | POSITIVE POLYSILANE PHOTORESIST MATERIALS AND METHOD FOR USE THEREOF |
US4548690A (en) * | 1984-02-28 | 1985-10-22 | Minnesota Mining And Manufacturing Company | Photoactivated polymerization of vinyl monomers in the presence of polysilanes and amines |
US4587205A (en) * | 1984-04-05 | 1986-05-06 | The United States Of America As Represented By The United States Department Of Energy | Method of using polysilane positive photoresist materials |
EP0212485A2 (en) * | 1985-08-16 | 1987-03-04 | Teijin Limited | Process for producing shaped silicon carbide article from the same |
FR2614622A1 (en) * | 1987-05-02 | 1988-11-04 | Dow Corning Ltd | PROCESS FOR THE PREPARATION OF POLYSILANES |
US4783516A (en) * | 1983-03-31 | 1988-11-08 | Union Carbide Corporation | Polysilane precursors containing olefinic groups for silicon carbide |
EP0303616A4 (en) * | 1986-04-14 | 1989-01-26 | John M Zeigler | Methods for the synthesis of polysilanes. |
US4804731A (en) * | 1985-02-25 | 1989-02-14 | University Of Florida Research Foundation, Inc. | Method for crosslinking of polysilastyrene |
US4839451A (en) * | 1988-04-04 | 1989-06-13 | Xerox Corporation | Processes for the preparation of polysilylenes |
US4879334A (en) * | 1986-03-11 | 1989-11-07 | The Foundation: The Research Institute For Special Inorganic Materials | Organopolyarylsilanes, process for manufacturing the same and fibers comprising the same |
US4897229A (en) * | 1988-10-12 | 1990-01-30 | Teijin Limited | Process for producing a shaped silicon carbide-based ceramic article |
US4921880A (en) * | 1988-08-15 | 1990-05-01 | Dow Corning Corporation | Adhesion promoter for UV curable siloxane compositions and compositions containing same |
US5188864A (en) * | 1988-08-15 | 1993-02-23 | Dow Corning Corporation | Adhesion promoter for UV curable siloxane compositions and compositions containing same |
US5358674A (en) * | 1993-03-18 | 1994-10-25 | Dow Corning Corporation | Process for preparing ceramic fibers from polysiloxanes |
DE4201336C2 (en) * | 1991-02-25 | 1999-04-22 | Korea Inst Sci & Tech | Polysilamethylenosilanes and process for their preparation |
US20080051548A1 (en) * | 2005-02-16 | 2008-02-28 | Debbie Bailey | Reinforced Silicone Resin Film and Method of Preparing Same |
US20080115827A1 (en) * | 2006-04-18 | 2008-05-22 | Itn Energy Systems, Inc. | Reinforcing Structures For Thin-Film Photovoltaic Device Substrates, And Associated Methods |
US20080138525A1 (en) * | 2005-02-16 | 2008-06-12 | Debbie Bailey | Reinforced Silicone Resin Film and Method of Preparing Same |
US20090084427A1 (en) * | 2006-04-18 | 2009-04-02 | Anderson Nicole R | Copper Indium Diselenide-Based Photovoltaic Device And Method Of Preparing the Same |
US20090084428A1 (en) * | 2006-04-18 | 2009-04-02 | Thomas Duncan Barnard | Copper Indium Diselenide-Based Photovoltaic Device And Method Of Preparing The Same |
US20090090413A1 (en) * | 2006-04-18 | 2009-04-09 | Dimitris Elias Katsoulis | Cadmium Telluride-Based Photovoltaic Device And Method Of Preparing The Same |
US20090130463A1 (en) * | 2005-10-05 | 2009-05-21 | John Dean Albaugh | Coated Substrates and Methods for their Preparation |
US20090155577A1 (en) * | 2005-08-04 | 2009-06-18 | Nicole Anderson | Reinforced silicone resin film and method of preparing same |
US20090246499A1 (en) * | 2006-10-05 | 2009-10-01 | Dimitris Katsoulis | Silicone Resin Film and Method of Preparing Same |
US20090308437A1 (en) * | 2006-09-19 | 2009-12-17 | Itn Energy Systems, Inc. | Systems And Processes For Bifacial Collection And Tandem Junctions Using A Thin-Film Photovoltaic Device |
US20100015454A1 (en) * | 2006-12-20 | 2010-01-21 | Nicole Anderson | Glass Substrates Coated or Laminated With Multiple Layers of Cured Silicone Resin Compositions |
US20100015439A1 (en) * | 2006-12-20 | 2010-01-21 | John Fredrick Buether | Glass Substrates Coated or Laminated With Cured Silicone Resin Compositions |
US20100028643A1 (en) * | 2007-02-22 | 2010-02-04 | Bizhong Zhu | Reinforced Silicone Resin Films |
US20100051920A1 (en) * | 2006-12-20 | 2010-03-04 | Dow Corning Corporation | Composite Article Including a Cation-Sensitive Layer |
US20100062247A1 (en) * | 2006-01-19 | 2010-03-11 | Mark Fisher | Silicone Resin Film, Method of Preparing Same, and Nanomaterial-Filled Silicone Composition |
US20100068538A1 (en) * | 2005-12-21 | 2010-03-18 | Dow Corning Corporation | Silicone Resin Film, Method of Preparing Same, and Nanomaterial-Filled Silicone Composition |
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US20100086760A1 (en) * | 2007-02-22 | 2010-04-08 | Bizhong Zhu | Reinforced Silicone Resin Films |
US20100093242A1 (en) * | 2007-02-22 | 2010-04-15 | Dimitris Elias Katsoulis | Composite Article Having Excellent Fire Resistance |
US20100104877A1 (en) * | 2007-02-22 | 2010-04-29 | Bizhong Zhu | Composite Article Having Excellent Fire and Impact Resistance and Method Of Making The Same |
US20100112321A1 (en) * | 2007-02-06 | 2010-05-06 | Dow Corning Corporation | Silicone Resin, Silicone Composition, Coated Substrate, and Reinforced Silicone Resin Film |
US20100129625A1 (en) * | 2007-05-01 | 2010-05-27 | Bizhong Zhu | Reinforced Silicone Resin Film |
US20100143686A1 (en) * | 2007-05-01 | 2010-06-10 | Bizhong Zhu | Nanomaterial-Filled Silicone Composition and Reinforced Silicone Resin Film |
US20100146886A1 (en) * | 2007-02-22 | 2010-06-17 | Bizhong Zhu | Composite Article Having Excellent Fire Resistance |
US20100184904A1 (en) * | 2007-10-12 | 2010-07-22 | Bizhong Zhu | Aluminum Oxide Dispersion and Method of Preparing Same |
US20100209687A1 (en) * | 2007-10-12 | 2010-08-19 | Bizhong Zhu | Reinforced Silicone Resin Film and Nanofiber-Filled Silicone Composition |
US20100273011A1 (en) * | 1996-12-20 | 2010-10-28 | Bianxiao Zhong | Silicone Composition, Silicone Adhesive, Coated and Laminated Substrates |
US20100316876A1 (en) * | 2008-03-04 | 2010-12-16 | Bizhong Zhu | Borosiloxane Composition, Borosiloxane Adhesive, Coated and Laminated Substrates |
US20110027584A1 (en) * | 2008-03-04 | 2011-02-03 | Bianxiao Zhong | Silicone Composition, Silicone Adhesive, Coated and Laminated Substrates |
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US4052430A (en) * | 1975-04-26 | 1977-10-04 | The Research Institute For Iron, Steel And Other Metals Of The Tohoku University | Method for producing organosilicon high molecular weight compounds having silicon and carbon as main skeleton components and said organosilicon high molecular weight compounds |
US4177230A (en) * | 1978-06-02 | 1979-12-04 | The United States Of America As Represented By The Secretary Of The Air Force | Process for producing reaction sintered silicon nitride of increased density |
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-
1981
- 1981-04-29 US US06/258,663 patent/US4324901A/en not_active Expired - Fee Related
-
1982
- 1982-03-19 WO PCT/US1982/000357 patent/WO1982003862A1/en unknown
- 1982-03-19 EP EP82901331A patent/EP0077794A1/en not_active Withdrawn
- 1982-03-19 GB GB08232287A patent/GB2112009A/en not_active Withdrawn
- 1982-04-09 IT IT48210/82A patent/IT1147840B/en active
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Cited By (81)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4783516A (en) * | 1983-03-31 | 1988-11-08 | Union Carbide Corporation | Polysilane precursors containing olefinic groups for silicon carbide |
US4548690A (en) * | 1984-02-28 | 1985-10-22 | Minnesota Mining And Manufacturing Company | Photoactivated polymerization of vinyl monomers in the presence of polysilanes and amines |
US4587205A (en) * | 1984-04-05 | 1986-05-06 | The United States Of America As Represented By The United States Department Of Energy | Method of using polysilane positive photoresist materials |
US4588801A (en) * | 1984-04-05 | 1986-05-13 | The United States Of America As Represented By The United States Department Of Energy | Polysilane positive photoresist materials and methods for their use |
DE3511615A1 (en) * | 1984-04-05 | 1985-10-17 | United States Department Of Energy, Washington, D.C. | POSITIVE POLYSILANE PHOTORESIST MATERIALS AND METHOD FOR USE THEREOF |
US4804731A (en) * | 1985-02-25 | 1989-02-14 | University Of Florida Research Foundation, Inc. | Method for crosslinking of polysilastyrene |
US4826892A (en) * | 1985-08-16 | 1989-05-02 | Teijin Limited | Polycarbosilastyrene copolymer, method for producing the same, and process for producing shaped silicon carbide article from the same |
EP0212485A3 (en) * | 1985-08-16 | 1988-06-15 | Teijin Limited | Process for producing shaped silicon carbide article from the same |
US4743411A (en) * | 1985-08-16 | 1988-05-10 | Teijin Limited | Process for producing shaped silicon carbide article from a polycarbosilastyrene copolymer |
EP0212485A2 (en) * | 1985-08-16 | 1987-03-04 | Teijin Limited | Process for producing shaped silicon carbide article from the same |
US4879334A (en) * | 1986-03-11 | 1989-11-07 | The Foundation: The Research Institute For Special Inorganic Materials | Organopolyarylsilanes, process for manufacturing the same and fibers comprising the same |
EP0303616A4 (en) * | 1986-04-14 | 1989-01-26 | John M Zeigler | Methods for the synthesis of polysilanes. |
EP0303616A1 (en) * | 1986-04-14 | 1989-02-22 | ZEIGLER, John M. | Methods for the synthesis of polysilanes |
FR2614622A1 (en) * | 1987-05-02 | 1988-11-04 | Dow Corning Ltd | PROCESS FOR THE PREPARATION OF POLYSILANES |
US4839451A (en) * | 1988-04-04 | 1989-06-13 | Xerox Corporation | Processes for the preparation of polysilylenes |
US5188864A (en) * | 1988-08-15 | 1993-02-23 | Dow Corning Corporation | Adhesion promoter for UV curable siloxane compositions and compositions containing same |
US4921880A (en) * | 1988-08-15 | 1990-05-01 | Dow Corning Corporation | Adhesion promoter for UV curable siloxane compositions and compositions containing same |
US4897229A (en) * | 1988-10-12 | 1990-01-30 | Teijin Limited | Process for producing a shaped silicon carbide-based ceramic article |
DE4201336C2 (en) * | 1991-02-25 | 1999-04-22 | Korea Inst Sci & Tech | Polysilamethylenosilanes and process for their preparation |
US5358674A (en) * | 1993-03-18 | 1994-10-25 | Dow Corning Corporation | Process for preparing ceramic fibers from polysiloxanes |
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US20090090413A1 (en) * | 2006-04-18 | 2009-04-09 | Dimitris Elias Katsoulis | Cadmium Telluride-Based Photovoltaic Device And Method Of Preparing The Same |
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Also Published As
Publication number | Publication date |
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GB2112009A (en) | 1983-07-13 |
IT8248210A0 (en) | 1982-04-09 |
WO1982003862A1 (en) | 1982-11-11 |
EP0077794A1 (en) | 1983-05-04 |
IT1147840B (en) | 1986-11-26 |
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